US11912736B2ActiveUtilityA1

Diaryl trehalose compounds and uses thereof

59
Assignee: THE UNIV OF MONTANAPriority: Feb 21, 2018Filed: Feb 21, 2019Granted: Feb 27, 2024
Est. expiryFeb 21, 2038(~11.6 yrs left)· nominal 20-yr term from priority
Inventors:David BurkhartGeorge EttengerJay EvansKendal T. RyterAlyson Smith
C07H 13/08A61K 39/04A61K 39/39A61P 37/04C07H 15/04C07H 13/04
59
PatentIndex Score
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Cited by
68
References
19
Claims

Abstract

Disclosed herein are diaryl trehalose compounds and methods of use thereof, for example as vaccine adjuvants.

Claims

exact text as granted — not AI-modified
What is claimed is: 
     
       1. A compound selected from the group consisting of:
 6,6′-bis(3,5-diethoxybenzoyl)-α,α-D-trehalose, 
 6,6′-bis(2-hydroxy-3,5-di-tert-butylbenzoyl)-α,α-D-trehalose, 
 6,6′-bis(3,5-dipentyloxybenzoyl)-α,α-D-trehalose, 
 6,6′-bis(3,4,5-triethoxybenzoyl)-α,α-D-trehalose, and 
 6,6′-bis(2,6-hydroxy-3,5-di-tert-butylbenzoylamino)-α,α-D-trehalose, 
 or a pharmaceutically acceptable salt thereof. 
 
     
     
       2. An adjuvant composition comprising an effective amount of a compound of  claim 1 , or a pharmaceutically acceptable salt thereof. 
     
     
       3. A vaccine composition comprising: (a) an antigen; and (b) an adjuvant composition comprising an effective amount of a compound of  claim 1 , or a pharmaceutically acceptable salt thereof. 
     
     
       4. The compound of  claim 1 , or a pharmaceutically acceptable salt thereof, wherein the compound is 6,6′-bis(3,5-diethoxybenzoyl)-α,α-D-trehalose. 
     
     
       5. A vaccine composition comprising: (a) an antigen; and (b) an adjuvant composition comprising an effective amount of the compound of  claim 4 , or a pharmaceutically acceptable salt thereof. 
     
     
       6. The compound of  claim 1 , or a pharmaceutically acceptable salt thereof, wherein the compound is 6,6′-bis(2-hydroxy-3,5-di-tert-butylbenzoyl)-α,α-D-trehalose. 
     
     
       7. A vaccine composition comprising: (a) an antigen; and (b) an adjuvant composition comprising an effective amount of the compound of  claim 6 , or a pharmaceutically acceptable salt thereof. 
     
     
       8. The compound of  claim 1 , or a pharmaceutically acceptable salt thereof, wherein the compound is 6,6′-bis(3,5-dipentyloxybenzoyl)-α,α-D-trehalose. 
     
     
       9. A vaccine composition comprising: (a) an antigen; and (b) an adjuvant composition comprising an effective amount of the compound of  claim 8 , or a pharmaceutically acceptable salt thereof. 
     
     
       10. The compound of  claim 1 , or a pharmaceutically acceptable salt thereof, wherein the compound is 6,6′-bis(3,4,5-triethoxybenzoyl)-α,α-D-trehalose. 
     
     
       11. A vaccine composition comprising: (a) an antigen; and (b) an adjuvant composition comprising an effective amount of the compound of  claim 10 , or a pharmaceutically acceptable salt thereof. 
     
     
       12. The compound of  claim 1 , or a pharmaceutically acceptable salt thereof, wherein the compound is 6,6′-bis(2,6-hydroxy-3,5-di-tert-butylbenzoylamino)-α,α-D-trehalose. 
     
     
       13. A vaccine composition comprising: (a) an antigen; and (b) an adjuvant composition comprising an effective amount of the compound of  claim 12 , or a pharmaceutically acceptable salt thereof. 
     
     
       14. A compound selected from the group consisting of: 
       
         
           
           
               
               
           
         
       
       and
 6,6′-bis(2-hydroxy-3,5-di-tert-butylbenzoylamino)-α,α-D-trehalose, 
 or a pharmaceutically acceptable salt thereof. 
 
     
     
       15. The compound of  claim 14 , or a pharmaceutically acceptable salt thereof, wherein the compound is 
       
         
           
           
               
               
           
         
       
     
     
       16. A vaccine composition comprising: (a) an antigen; and (b) an adjuvant composition comprising an effective amount of the compound of  claim 15 , or a pharmaceutically acceptable salt thereof. 
     
     
       17. The compound of  claim 14 , or a pharmaceutically acceptable salt thereof, wherein the compound is 6,6′-bis(2-hydroxy-3,5-di-tert-butylbenzoylamino)-α,α-D-trehalose. 
     
     
       18. A vaccine composition comprising: (a) an antigen; and (b) an adjuvant composition comprising an effective amount of the compound of  claim 17 , or a pharmaceutically acceptable salt thereof. 
     
     
       19. An adjuvant composition comprising an effective amount of a compound of  claim 14 , or a pharmaceutically acceptable salt thereof.

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